JPH02117673A - 新規環状アミジン及びその製造方法 - Google Patents

新規環状アミジン及びその製造方法

Info

Publication number: JPH02117673A
Authority: JP; Japan
Prior art keywords: formula; alkyl; hydrogen; formulas; tables
Prior art date: 1988-08-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP1215125A

Other languages

English (en)

Japanese (ja)

Inventor

Burkhard Dipl Chem Dr Koehler

ブルクハルト・ケーラー

Helmut-Martin Meier

ヘルムート‐マルテイン・マイアー

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-08-25

Filing date

1989-08-23

Publication date

1990-05-02

1989-08-23 Application filed by Bayer AG filed Critical Bayer AG

1990-05-02 Publication of JPH02117673A publication Critical patent/JPH02117673A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 6
-1 cyclic amidine Chemical class 0.000 title claims description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
239000003054 catalyst Substances 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
239000002904 solvent Substances 0.000 claims abstract description 6
229920003023 plastic Polymers 0.000 claims abstract description 3
239000004033 plastic Substances 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
150000001875 compounds Chemical class 0.000 abstract description 7
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
239000000463 material Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000002431 hydrogen Chemical group 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 1
SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 description 1
DIJSYXJZZFZHLA-UHFFFAOYSA-N 2-methoxy-1-azacyclotridecene Chemical compound COC1=NCCCCCCCCCCC1 DIJSYXJZZFZHLA-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
ZXPNHQOWDWPUEH-UHFFFAOYSA-N boric acid;sulfuric acid Chemical compound OB(O)O.OS(O)(=O)=O ZXPNHQOWDWPUEH-UHFFFAOYSA-N 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003470 sulfuric acid monoesters Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Compositions Of Macromolecular Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

JP1215125A 1988-08-25 1989-08-23 新規環状アミジン及びその製造方法 Pending JPH02117673A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3828759A DE3828759A1 (de)	1988-08-25	1988-08-25	Neue cyclische amidine und verfahren zu ihrer herstellung
DE3828759.5		1988-08-25

Publications (1)

Publication Number	Publication Date
JPH02117673A true JPH02117673A (ja)	1990-05-02

Family

ID=6361518

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1215125A Pending JPH02117673A (ja)	1988-08-25	1989-08-23	新規環状アミジン及びその製造方法

Country Status (3)

Country	Link
EP (1)	EP0355645B1 (de)
JP (1)	JPH02117673A (de)
DE (2)	DE3828759A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7632098B2 (en)	2003-08-12	2009-12-15	3M Innovative Properties Company	Self-adhesive dental compositions and methods

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2119163A1 (de) *	1970-04-24	1971-11-04	E.Gy.T. Gyogyszervegyeszeti Gyar, Budapest	Verfahren zur Herstellung von semicyclischen Amidinen
DE2029299C3 (de) *	1970-06-13	1980-08-21	Bayer Ag, 5090 Leverkusen	Neue Aminophenylamidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE3529692A1 (de) *	1985-08-20	1987-02-26	Bayer Ag	Verwendung von lactamamiden als leistungsfoerderer bei tieren

1988
- 1988-08-25 DE DE3828759A patent/DE3828759A1/de not_active Withdrawn
1989
- 1989-08-12 EP EP89114978A patent/EP0355645B1/de not_active Expired - Lifetime
- 1989-08-12 DE DE58907558T patent/DE58907558D1/de not_active Expired - Fee Related
- 1989-08-23 JP JP1215125A patent/JPH02117673A/ja active Pending

Also Published As

Publication number	Publication date
EP0355645A3 (de)	1991-10-02
EP0355645B1 (de)	1994-04-27
DE3828759A1 (de)	1990-03-01
DE58907558D1 (de)	1994-06-01
EP0355645A2 (de)	1990-02-28

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